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Identification
NameThenoyltrifluoroacetone
Accession NumberDB04795
TypeSmall Molecule
GroupsExperimental
Description

Thenoyltrifluoroacetone is a chelating agent and inhibitor of cellular respiration. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
.alpha.-ThenoyltrifluoroacetoneNot AvailableNot Available
1-Thenoyl-3,3,3-trifluoroacetoneNot AvailableNot Available
1,1,1-Trifluoro-3-(2-thenoyl)acetoneNot AvailableNot Available
2-ThenoyltrifluoroacetoneNot AvailableNot Available
alpha-ThenoyltrifluoroacetoneNot AvailableNot Available
Perfluoroacetyl(2-thenoyl)methaneNot AvailableNot Available
TTFANot AvailableNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
Categories
CAS number326-91-0
WeightAverage: 222.184
Monoisotopic: 221.996234709
Chemical FormulaC8H5F3O2S
InChI KeyTXBBUSUXYMIVOS-UHFFFAOYSA-N
InChI
InChI=1S/C8H5F3O2S/c9-8(10,11)7(13)4-5(12)6-2-1-3-14-6/h1-3H,4H2
IUPAC Name
4,4,4-trifluoro-1-(thiophen-2-yl)butane-1,3-dione
SMILES
FC(F)(F)C(=O)CC(=O)C1=CC=CS1
Mass Specshow(9.36 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassThiophenes
SubclassNot Available
Direct parentThiophenes
Alternative parentsKetones; Polyamines; Enolates; Organofluorides; Alkyl Fluorides
Substituentsketone; polyamine; enolate; organohalogen; organofluoride; carbonyl group; alkyl halide; alkyl fluoride
Classification descriptionThis compound belongs to the thiophenes. These are compounds containing a five-member aromatic compound made up of one sulfur atom and four carbon atoms.
Pharmacology
IndicationNot Available
PharmacodynamicsStudies indicate that thenoyltrifluoroacetone is a potent inhibitor of carboxylesterase activity, in addition to its ability to inhibit mitochondrial complex II activity.
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 1.0
Blood Brain Barrier + 0.9964
Caco-2 permeable + 0.537
P-glycoprotein substrate Non-substrate 0.8104
P-glycoprotein inhibitor I Non-inhibitor 0.7748
P-glycoprotein inhibitor II Non-inhibitor 0.783
Renal organic cation transporter Non-inhibitor 0.8788
CYP450 2C9 substrate Non-substrate 0.8094
CYP450 2D6 substrate Non-substrate 0.8448
CYP450 3A4 substrate Non-substrate 0.7506
CYP450 1A2 substrate Non-inhibitor 0.6133
CYP450 2C9 substrate Inhibitor 0.582
CYP450 2D6 substrate Non-inhibitor 0.7097
CYP450 2C19 substrate Inhibitor 0.7893
CYP450 3A4 substrate Non-inhibitor 0.7544
CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5302
Ames test Non AMES toxic 0.5586
Carcinogenicity Non-carcinogens 0.6418
Biodegradation Not ready biodegradable 0.8573
Rat acute toxicity 2.7650 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9736
hERG inhibition (predictor II) Non-inhibitor 0.9203
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point42 °CPhysProp
boiling point96-98 °C at 8.00E+00 mm HgPhysProp
logP1.46HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0752ALOGPS
logP2.37ALOGPS
logP2.8ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)7.17ChemAxon
pKa (Strongest Basic)-8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity44.26 m3·mol-1ChemAxon
Polarizability16.74 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General Reference
  1. Zhang JG, Fariss MW: Thenoyltrifluoroacetone, a potent inhibitor of carboxylesterase activity. Biochem Pharmacol. 2002 Feb 15;63(4):751-4. Pubmed
External Links
ResourceLink
PubChem Compound5601
PubChem Substance46504456
HETTTF
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Liver carboxylesterase 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Liver carboxylesterase 1 P23141 Details

References:

  1. Zhang JG, Fariss MW: Thenoyltrifluoroacetone, a potent inhibitor of carboxylesterase activity. Biochem Pharmacol. 2002 Feb 15;63(4):751-4. Pubmed
  2. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

2. Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial P31040 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

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Drug created on September 11, 2007 11:49 / Updated on September 16, 2013 17:25